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Synthesis of 6,12‐Methanobenzo[ d ]pyrano[3,4‐ g ][1,3]dioxocin‐1(12 H )‐ones and Study of Their Interaction with DNA and β‐Lactoglobulin
Author(s) -
Sepay Nayim,
Guha Chayan,
Maity Sanhita,
Mallik Asok K.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701224
Subject(s) - chemistry , domino , pyran , polystyrene , catalysis , sequence (biology) , stereochemistry , dna , combinatorial chemistry , organic chemistry , polymer , biochemistry
An efficient synthesis of 6,12‐methanobenzo[ d ]pyrano[3,4‐ g ][1,3]dioxocin‐1(12 H )‐ones, a new class of 2,8‐dioxabicyclo[3.3.1]nonanes, starting from 2‐hydroxychalcones or their analogues and 4‐hydroxy‐6‐methyl‐2 H ‐pyran‐2‐one has been achieved by use of amberlyst‐15, a sulfonated polystyrene resin, as a recyclable heterogeneous catalyst. The methodology involves a domino sequence of Michael addition and two‐stage heterocyclization. Among the synthesized products, two show significant ct‐DNA‐binding properties and all show strong binding with the carrier protein β‐lactoglobulin (β‐lg). A study of antibacterial properties conducted on two bacterial species by using four compounds showed that two of them are moderately active.